Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom
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- 作者：Yahia Nasser Mabkhot (1)
Assem Barakat (1) (2)
Abdullah Mohammed Al-Majid (1)
Saeed Alshahrani (1)
Sammer Yousuf (3)
M Iqbal Choudhary (1) (3) - 关键词：Thienothiophene ; Oxazole ; Imidazole ; Thiazole ; Bisheterocycles ; β ; glucuronidase inhibition ; α ; glucosidase inhibition ; DPPH radical scavenging activity ; Ctotoxicity ; Cancer cell line
- 刊名：Chemistry Central Journal
- 出版年：2013
- 出版时间：December 2013
- 年：2013
- 卷：7
- 期：1
- 全文大小：240 KB
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Assem Barakat (1) (2)
Abdullah Mohammed Al-Majid (1)
Saeed Alshahrani (1)
Sammer Yousuf (3)
M Iqbal Choudhary (1) (3)
1. Department of Chemistry, Faculty of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia
2. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, 21321, Alexandria, Egypt
3. H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi, 75270, Pakistan - ISSN：1752-153X
文摘
Background The derivatives of thieno[2,3-b]thiophene belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial application. Results A new building block with two electrophilic center of thieno[2,3-b]thiophene derivatives 2 has been reported by one-pot reaction of diketone derivative 1 with Br2/AcOH in excellent yield. A variety of heteroaromatics having bis(1H-imidazo[1,2a] benzimidazole), bis(1H-imidazo[1,2-b][1,2,4]triazole)-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives, dioxazolo-, dithiazolo-, and 1H-imidazolo-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives as well pyrrolo, thiazolo -3-methyl-4-phenylthieno[2,3-b]thiophene derivatives have been designed, synthesized, characterized, and evaluated for their biological activity. Compounds 3-strong class="a-plus-plus">9 showed good bioassay result. These new derivatives were evaluated for anti-cancer activity against PC-3 cell lines, in vitro antioxidant potential and β-glucuronidase and α-glucosidase inhibitory activities. Compound 3 (IC50--6.26?±-.18-em class="a-plus-plus">μM) showed a potent DPPH radical scavenging antioxidant activity and found to be more active than standard N-acetylcystein (IC50--05.9?±-.1-em class="a-plus-plus">μM). Compounds 8a (IC50--3.2?±-.34-em class="a-plus-plus">μM) and 8b (IC50--4.1?±-.28-em class="a-plus-plus">μM) found as potent inhibitor of α-glucusidase several fold more active than the standard acarbose (IC50--41?±-.73-em class="a-plus-plus">μM). Most promising results were obtained in β-glucuronidase enzyme inhibition assay. Compounds 5 (IC50--.13?±-.019-em class="a-plus-plus">μM), 6 (IC50--9.9?±-.285-em class="a-plus-plus">μM), 8a (IC50--.2?±-.0785-em class="a-plus-plus">μM) and 9 (IC50--.003?±-.09-em class="a-plus-plus">μM) showed a potent inhibition of β-glucuronidase. Compound 9 was found to be several hundred fold more active than standard D-Saccharic acid 1,4-lactone (IC50--5.75?±-.16-em class="a-plus-plus">μM). Conclusions Synthesis, characterization, and in vitro biological activity of a series of thieno[2,3-b]thiophene have been investigated.